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New trans-A2B2-porphyrins substituted at phenyl positions were synthesized from 4-methylphthalic acid as a starting material through sequential multistep reactions. These macrocycles were characterized by 1H NMR, 13C NMR, 19F NMR, 1H-1H COSY NMR, and MALDI-TOF mass spectrometry. Computational studies were performed on the porphyrins to investigate various factors such as structural features, electronic energy, energy gaps, and aromaticity. Energy band gap values of these compounds especially N-hydroxyphthalimide-functionalized porphyrins were small that makes them as good candidates for solar cell systems and photocatalysis. Relationships between electronic energies and aromaticity of the compounds were then investigated. The data indicated that the aromaticity features at the center of two series of these compounds (fluorinated and non-fluorinated porphyrins) were in the opposite manner.


Ali Reza Oveisi, Pouya Karimi, Hojat Samareh Delarami, Saba Daliran, Ahmad Khorramabadi-Zad, Mostafa Khajeh, Esmael Sanchooli, Mansour Ghaffari-Moghaddam. New porphyrins: synthesis, characterization, and computational studies. Molecular diversity. 2020 May;24(2):335-344

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PMID: 31062142

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